Although studies claim increases in underrepresented populations choosing STEM majors, barriers to retention, and higher education degree completion in STEM still exist. This study examined efforts of a prominent technical university to attract and retain urban high school graduates through a tuition scholarship program. We sought to determine the trajectories of recruited urban high school graduates and explored students reasoning behind their choice of STEM majors. Findings revealed unforeseen obstacles prohibiting students from pursuing STEM degrees despite free tuition and other benefits of the diversity recruitment program. Student obstacles included: (i) logistic barriers; (ii) academic resources access; and (iii) social/cultural support. A secondary but related finding was the self-realization of engineering faculty culpability in the attrition they observed. This critical account of race and privilege told by insiders to the engineering discipline speaks directly to the failure of educational institutions to address essential components of the economic and academic segregation which currently exists against a backdrop of reform calls which aim to diversify the engineering workforce. Implications for future research and recruitment efforts are discussed.